Before Open Enrollment Starts: 7 Questions Employers Need to Answer
By VICKY BROWN
If your open enrollment strategy is “wait for the renewal packet and figure it out,” here’s the truth. You don’t have a strategy. You have a deadline. And that’s exactly why this time of year feels like a scramble instead of a decision you were actually prepared to make.
Here’s the thing about an Open Enrollment Checklist for employers that most people get backwards. Open enrollment isn’t a benefits administration task where you just process paperwork and move on. It’s a decision design exercise, and it happens well before your employees ever see a single form. You’re about to ask your team to choose their coverage for the next twelve months, medical, dental, vision, maybe some voluntary benefits stacked on top. But before you hand them that decision, you need to have made several of your own. Most employers skip straight past that part. They wait for the packet from the broker, glance at the increase, and figure out what to do about it in about a week and a half. That’s not planning. That’s reacting to an invoice.
So let’s walk through what actually needs to happen first.
Does your benefit package still fit the team you have
A lot of companies keep renewing the same plans year after year without ever asking whether the people underneath those plans have changed. Maybe you had twelve employees when you first built this lineup, and now you’ve got forty five. Maybe more of your team has kids now, or you’ve gotten younger, or older, or hired across pay levels that look nothing like where you started. The real question isn’t whether you can renew what you already have. It’s whether, if you were building your benefits program from scratch for the team sitting in front of you right now, you’d build this same thing. That’s a more honest conversation, and it’s one worth having before renewal season, not during it.
Know why you’re offering benefits in the first place
This step gets skipped more than any other on any real Open Enrollment Checklist for employers. Are you offering benefits to meet a baseline expectation? To recruit? To retain people you’ve already invested time and training into? To protect your team from a catastrophic medical bill? To compete for a specific kind of talent in a specific market? You don’t need a mission statement here. You need clarity, because once you know why you’re spending the money, you can actually evaluate whether what you’re offering is doing its job. Skip this step, and renewal turns into “the increase is eleven percent, what can we cut,” which isn’t a strategy at all.
Look past what the plan costs you and toward what it costs your employee
Checking that payroll deductions are correct is a math problem. This is a design problem, and it’s a different one. A company can hold the employee contribution flat and feel good about it, while quietly shifting everyone into a plan with a much higher deductible, steeper prescription costs, or a narrower network. From where you’re sitting, that plan looks affordable. From where your employee is sitting, it just got a lot more expensive the first time they actually need care. That doesn’t automatically mean you made the wrong call. Small businesses have real budgets, and every choice comes with a tradeoff somewhere. Just make that call with your eyes open, not from an employee’s complaint six months later.
“… You need clarity, because once you know why you’re spending the money, you can actually evaluate whether what you’re offering is doing its job“
Ask what your team actually struggled with last year
Don’t just ask your broker for the new rates. Ask yourself what you already know. Were people confused about how a deductible works. Did they struggle to find an in-network provider. Were there constant issues at the pharmacy counter. Did nobody understand the HSA well enough to actually use it, so now there’s a pile of unused funds and a pile of confused employees. You probably don’t need a forty question survey to answer this. Whoever administers benefits day to day at your company already knows exactly where the friction has been, because they’ve been hearing about it for eleven months straight.
Decide whether you’re offering choice or just complexity
Business owners sometimes assume more options automatically means a better package. Three medical plans, two dental plans, two vision plans, voluntary life, accident, critical illness, hospital indemnity, an FSA, an HSA, an EAP, telehealth, legal services. Now your employee is staring at seventeen PDFs trying to figure out whether they personally need hospital indemnity coverage, with nobody explaining how to even think about it. More choice isn’t automatically bad. But every option you add is one more decision somebody has to understand well enough to make correctly. So ask whether each item on the list has a clear purpose, and whether you can explain who it might make sense for without crossing the line into picking for them.
Whether you’re an entrepreneur jumping into a leadership role, a seasoned business pro with new HR responsibilities, or just starting your HR career – we’ve got the right path to guide you through your HR hurdles.
Check out the Leaders Journey Experience.
Decide how you’re going to communicate the tradeoffs
This is different from checking whether the numbers reconcile after the fact. This is about whether your employees will actually understand the decision you’re asking them to make right now. If premiums went up, say so plainly. If the company absorbed part of the increase, say that too. If the deductible went up specifically to keep the paycheck impact manageable, explain that tradeoff out loud instead of hoping nobody notices.
And here’s where the line matters most. Educate without advising. You can explain what a deductible does. You can explain how coinsurance works. What you shouldn’t do is look at an employee and tell them which plan to pick because you’ve decided you know their situation better than they do. That call belongs to them, based on their own life and their own risk tolerance. Your job is making sure they actually understand what they’re choosing, not choosing it for them.
Decide who owns what happens after enrollment closes
Open enrollment doesn’t actually end the moment everyone hits submit. Someone has to review the elections that never got completed. Someone has to follow up with employees who didn’t enroll at all. Someone has to verify dependent documentation, confirm the carrier received the feed correctly, and check the first payroll deduction against what was actually elected. Everyone enrolled and everyone is correctly covered are not the same sentence, and the gap between those two sentences is exactly where things tend to go wrong quietly, for months, before anyone notices.
Open enrollment shouldn’t start with “here are this year’s plans, go pick one.” It should start weeks earlier, with you asking what you’re actually trying to offer, what you can genuinely afford, and what your team needs to understand before they’re asked to decide anything. Your employees have a decision to make once enrollment opens. But you have several to make first, and if you haven’t answered them yet, you’re not actually ready to ask your team to answer theirs.